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FOR SALE: 3 Bedroom 1 Full Bath Rancher with Nice Sized Back Yard and Screened in Porch. Home Features Living Room, Eat in Kitchen, Three Bedrooms, One Full Bath, Laundr...

HUD home SOLD STRICTLY AS IS . Calling all investors and homeowners with an eye for opportunity! Uncover the untapped potential at 203 Radcliffe Dr, Chestertown, MD - a p...

Excellent Location! This charming 3-bedroom, 1-bathroom bungalow sits proudly along one of Chestertown's primary roads. Positioned in an Intense Village zone, it caters t...

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Introducing this stunning new construction home just outside of Chestertown, MD in the Blakefield community ( QA Side) Boasting 3 bedrooms and 2.5 baths, this modern res...

Location, location, location! Located in College Heights and just a few short blocks from Washington College and a few more blocks from shopping and downtown Historic Ch...

Welcome to your dream country home! This charming property, nestled in a serene rural setting, offers the perfect blend of modern comfort and rustic allure. Boasting thre...

Completely remodeled, solid brick rancher sitting on a half-acre of land with a detached 1 car garage. Located just outside of Chestertown, this home is completely remod...

"Strawboard Mill" offers 2 brick, townhomes (each townhouse has 2 units), with metal roofs, 1 efficiency apartment and a 3 bedroom, 2 bath residence. The brick townhome...

Split-level home nestled in a serene wooded area, minutes from the Chester River. Ample garage parking, expansive deck, and untapped potential on a generous lot. This is ...

Beautiful Dutch Colonial on 3 Acres with 500 +/- feet of waterfront overlooking Worton Creek. Near Worton Creek Marina and only a short drive to Historic Chestertown or ...

This former horse barn was converted in 1990 into a well-crafted personal residence. In early 2018, the current stewards retained acclaimed contractors Taylor Loughry to ...

OPEN HOUSE IS CANCELLED FOR 11/11/23 Escape to your own rural paradise with this exceptional 3-4 bedroom retreat that seamlessly blends modern comfort with the tranquilit...

"Strawboard Mill" offers 2 brick townhomes, with metal roofs, 1 efficiency apartment and a 3 bedroom, 2 bath residence. The brick townhomes were built in 1902+/- and wer...

Come by this AWESOME, RENOVATED Rancher in the WATERFRONT Community of Chesapeake Landing is Chestertown. This beautifully renovated single level home is ready for it's n...

The only available under-construction interior townhome in The Village at Chestertown that backs to community open space with pond views! This two-story Jefferson is an o...

Welcome to this charming 3-bedroom, 1-bathroom Ranch-style home, designed for convenient single-level living. Situated on a corner lot with a screened back porch and fenc...

Beautiful cape on a half acre with an attached garage in the great neighborhood of Coventry Farms. No HOA. A huge addition on the back of the house provides lots of ext...

Come by this lovely BRAND NEW middle unit home in a Triplex in Historic Chestertown, available for move in in October. This home features Luxury Vinyl Flooring through...

Main Level Features Dining Room, Living Room, Family Room, Kitchen with Breakfast Nook Bump Out, Laundry Room, Half Bath, and Den. Upper Level Features Large Primary Bed...

Prime historic district location! This fully furnished, prominent Church Alley address is completely turn-key for your immediate enjoyment! Circa 1880, 104 Church Alley...

The only available under-construction interior townhome in The Village at Chestertown with pond views! This two-story Jefferson is an open-concept townhome with three bed...

Currently the only under-construction end-of-unit townhome available in The Village at Chestertown with pond views! This two-story Jefferson is an open-concept townhome w...

Endless possibilities for this centrally located property in Chestertown, across from Kent Plaza Shopping Center and close to Washington College and the newly built YMCA....

Endless opportunities for this centrally located property in Chestertown, across from Kent Plaza Shopping Center and close to Washington College, Dixon Valve, and the ne...

Affordable Living Minutes From Chestertown. Enjoy all of Chestertown’s charm and amenities without Chestertown taxes in the desirable and quiet community of Chester Harbo...

Great home located in desired Coventry Farms community of Chestertown. This home offers plenty of space for entertaining boasting 4 bedrooms, 21/2 baths, master suite, la...

Welcome to 101 S. Kent St! Prepare to be charmed by this beautifully updated and lovingly maintained historic home, located on a peaceful and quaint street. Built in 188...

This incredible home with seasonal water views of the Chester River is positioned on a private lot on Aldan Dr in Chestertown. Inside the beautiful foyer are gleaming h...

Within steps of the Chester River, this updated and renovated farmhouse is filled with character and charm. The light filled rooms, cozy interior and newly added family r...

This remarkable 4BR/3.5BA waterfront home boasts historic elegance and beautiful water views! The best of both worlds, this property is located on the Chester River, off...

Amazing 4 Acre Waterfront Opportunity awaits a new owner who is willing to update the adorable cape with large wrap around deck that overlooks the Chester River. Enjoy ...

Spacious, well-situated 3 or 4 bedroom, 2.5 bathroom rambler on almost 3/4 of an acre just outside downtown Chestertown. Sit on the front or back porches and enjoy the p...

Come by this lovely BRAND NEW town home in Historic Chestertown, available for move in by early November. This home features Luxury Vinyl Flooring throughout, White Shak...

Welcome to this newly renovated home with stunning upgrades throughout! This charming, easy-living home, in Chestertown, MD has all new LVP flooring, paint and drywall, ...

Whether you envision building your dream home or are seeking a hunting retreat, this secluded lot offers options. Situated on 42.598 acres of select cut woodland, this p...

This pre-1900 rowhouse over-looking the Chester River and situated on South Water Street was expanded in 2013 to maximize its water-view living, both indoors and outdoors...

One of the last available 1920s houses available in downtown Chestertown that is ready to be lived in and priced to support a 21st century renovation and possible expansi...

Welcome to Your Forever Home! Step into luxury with over 3,000 sqft of living space, and that's just the beginning. As you explore this exquisite property, you'll discov...

This contemporary waterfront property offers the perfect blend of modern living and waterfront serenity. The open floor plan affords views of Mill Creek from every room....

This cottage on Fairlee Creek is simpy adorable!!In a protected cove with a quick run to the Bay. Love the feel of this open home with a huge back screened in porch. This...

Nestled within the desirable community of College Heights, this charming Colonial-style home offers the perfect blend of classic design and modern convenience. Step insid...

Custom built house on the East Fork of Langford Creek set on 8+ acres with a private dock. This is the first time the house has been for sale; original owners. It was bu...

Priced To Sell Fast! Charming Updated 1 Level Rambler, Spacious Kitchen with QUARTZ Counters, Stainless Steel Appliances, Spacious Bedrooms, New Custom Paint, Updated Bat...

Bask in the beauty of this incredible 1920s home in downtown Chestertown! At 2890 square feet, this freshly painted 5 bedroom, 3.5 bathroom property has tons of space and...

THIS CHARMING HOME OFFERS A COZY LIVING SPACE THAT MAXIMIZES EFFICIENCY! BRAND NEW ROOF INSTALLED ON 10/18/23! Its modern 2023 renovations provide an inviting atmosphere ...

This hidden gem is ready for its new owner!

Lot 5- A one acre building lot in the desirable Prestwick community on the golf course. No builder tie-in. Public sewer and well water. Surrounded by mature beech trees. ...

**Red Tag Sales Event through October 22, 2023! Was $251,990 Now: $249,470!** New townhome, under construction in the Village at Chestertown! This two-story Jefferson is...